


Handsy

by discount67



Series: A Series Of Fortunate Events [3]
Category: Supernatural
Genre: Blow Jobs, Come Swallowing, First Time Blow Jobs, First Time Hand Jobs, Fluff, Fluff and Smut, French Kissing, Hand Jobs, Kissing, M/M, Making Out, Masturbation, Oral Sex, Smut
Language: English
Status: Completed
Published: 2020-08-05
Updated: 2020-08-05
Packaged: 2021-03-06 06:09:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,191
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25718599
Author URL: https://archiveofourown.org/users/discount67/pseuds/discount67
Summary: Jack wants to break the no-hands rule, needing to feel Sam under his fingertips. Things escalate and the boys use something more than just their hands to please each other.
Relationships: Jack Kline & Sam Winchester, Jack Kline/Sam Winchester
Series: A Series Of Fortunate Events [3]
Series URL: https://archiveofourown.org/series/1841971
Comments: 4
Kudos: 42





	Handsy

Sam found Jack nestled in bed. It was 1 AM, Jack's silhouette casting a shadow on the floor of the dimly lit room. He wasn't asleep, just lost in thought. He hadn't come out to eat or talk to anyone, and it worried Castiel and Dean. He had been avoiding Castiel, he couldn't bring himself to look at the angel's worried face. Dean didn't pry when Jack said he was fine, he just sent Sam over the second he arrived home. Jack felt bad for worrying everyone like this, but he was working up to something big.

Castiel and Dean were becoming aware of what was going on between Sam and Jack, realizing they shared something special. When Dean couldn't find Sam in his room, he'd find him over in Jack's room relaxing on the bed together. It was a situation none of the men ever spoke of, and their days went on like usual. Everyone knew Sam would never hurt Jack. Sam smiled more often and Jack's eyes gleamed with contentment, and that's all that mattered. 

Thinking of past conversations, Jack gathered his courage. He and Sam shared their love for each other, vowing to explore their feelings before they made it official. They'd spend whole afternoons in bed making out and enjoying each others bodies, it was almost painful to let go of one another. Jack ached for more, he wanted to prove his love for Sam in a way they had never before. 'Baby steps' he was told. Jack felt like was ready for the next step.

Jack sat up as Sam approached him, the corners of his lips twitched nervously as he tried to smile. Sam raised his eyebrows, it was quite obvious something was off, he just didn't know what it was yet. He raised his hand to sweep locks of dirty blond hair out of the Nephilim's face, leaning in to press a soft kiss to his cheek. “Jack, what's going on? Dean and Cass are worried about you.” Sam asked softly.

“I just have something to ask you,” Sam relaxed at Jack's words, visibly relieved that nothing serious was going on. Jack knew he was going to be scolded later for stressing everyone out, but that wasn't the matter at hand now. He inhaled, not knowing how to bring it up without being shy. “I, um- I want to try something new.” Jack uttered.

Sam nodded slowly, he understood where this was going. They had previously talked it over, how Jack was maturing and becoming ready to do more than kissing and masturbating mutually. Sam's rule of not using their hands on each other was for Jack's own protection, as a lot of things were still new for him. He'd leave Jack the space to bring it up himself when he felt ready, and after some months it looked like he was.

Jack's cheeks were cherry red, the nervousness had subsided and excitement took its place. “I've been thinking about it,” he started, trailing off when Sam stared at him. “...can we try touching each other?” he finished.

This was something Sam had to think about before agreeing. He had to be sure Jack was genuinely ready. Jack looked up at him with hopeful eyes, visibly hoping he'd get a yes. 

“Yeah. I'm happy you told me, we can try tomorrow.” Sam offered, he wanted to pick the perfect time to make the experience perfect. However, this didn't satisfy Jack. The younger man crawled closer to Sam as he shook his head.

“Not now? I waited until now to ask you, Dean and Castiel went to their rooms.” Jack whispered, eyes darting to the door implying nobody was around. 

Sam chuckled. “You really thought this through, huh?” He said, snorting when Jack nodded eagerly. Of course he did, it was true they were a bit more open towards everything, but nobody except them needed to know about what they did in the bedroom. The thought of having complete privacy during the night turned Sam on more than he'd care to admit. “You set the pace, Jack. I'll follow.”

Jack nodded and pushed back the covers he was lying on. He reached down to pull off his shirt, pale skin glowing in the dimmed lights. His abdominal muscles were slightly pronounced with small pink nipples placed perfectly on his chest. His skin looked so soft, Sam audibly gasped as he inspected the Nephilim's body. Jack stretched, flexing his back and neck as his muscles tightened. 

Sam couldn't take his eyes off. “God, Jack. You're so beautiful.” he murmured over and over again. He grabbed the hem of his own shirt to get it off as well. Sam's chest was well toned, a tan decorating the skin. Jack crawled over, eyes glowing as he looked at Sam's unclothed torso. He leaned down and let their chests touch gently, the sensation causing both men to inhale sharply. Their skin was hot and sensitive, and the room started to feel stuffy. They've been close in other ways, but skin on skin contact almost made Sam's eyes roll in the back of his head. It felt so good to be this close with somebody he loved so dearly. Jack buried his face in the crook of Sam's neck, his hand running over the goosebumps on his belly.

“Want to feel close to you,” Jack breathed, enjoying Sam's large hands caressing his sensitive skin. He reached for the older man's zipper, getting rewarded with a stifled groan as he bumped the hardness beneath the denim. “I wanna make you feel good.“

Sam felt like the luckiest man in the world. In his arms was a small Nephilim with eyes so full of lust and love they glowed gold. He nodded as he let Jack undo his zipper, stopping him as he tried to unbutton the garment fully. “I know you want to do this, but I'm responsible. Are you absolutely sure?” Sam asked clearly, he wanted every room for interpretation out of the way.

Nodding fervently, Jack leaned in to press a kiss to Sam's lips. The older man groaned as he grasped the back of Jack's neck, opening his mouth to deepen the kiss. The sensation of their tongues caused Jack to shiver, he wanted to bury himself in the heat that Sam's body was radiating and hide there forever. Sam used his free hand to undo the button Jack was struggling with, moaning into the kiss as the pressure on his erection subsided. Jack whimpered and pressed his waist into Sam's thigh. “Mine too.” he said, guiding Sam's hand to his own jeans. The weight of the Winchester's large hand on his crotch caused his mind to spiral as the item of clothing soon left his body. 

There lie Jack, curled up in Sam's arms with nothing more on his body than his boxers. He couldn't have imagined having it any other way, it felt so right. Jack felt shy from Sam's eyes on him, and the latter noticed. “You okay?” Sam asked, continuing to rub circles on Jack's skin when he whispered an affirmation. 

“Don't wanna be the only naked one.” Jack said, a soft smile on his face as Sam took off his pants to match Jack's bare state. Their cocks stood up fiercely below their underwear begging for attention, but they weren't going to give in just yet.

Sam placed his finger underneath Jack's chin and lifted up his head. He looked into bright gold eyes as he pressed his body into his. “You can tell me to stop any time, Jack.” he reassured the younger man, wanting him to feel comfortable. He placed a kiss on Jack's neck, moving lower with every sigh he let out. Jack dug his fingers into Sam's shoulders when he felt wet lips enveloping his nipple, the sensation buzzing in his chest sent shockwaves right to his erection. Sam groaned at the boy wiggling below him, enjoying how he reacted to every touch.

Tipping his head back, Jack called out Sam's name as his chest and abdomen got assaulted by his tongue. “Sam… Oh. Oh- that feels good,” Jack sighed as Sam used his nails to rake up and down his sides. 

“Yeah? You want more?”

“Please.”

With no time to waste, Sam lowered his head until his lips were resting against the waistband of Jack's underwear. He pressed his lips to the patch of skin below his belly button, gently using his teeth to nibble and suck along the sensitive flesh. Jack's heartbeat quickened as Sam let go of his hips and placed them at his inner thighs as he spread them open.

Jack panted and sighed as Sam worked his mouth along the milky skin, begging him to take off the underwear that was clearly in the way. Sam wanted to stretch the moment a little longer, sucking hickeys into the soft skin until Jack cried out. “Sam, please! I need it.” he ordered the older man. Sam laughed heartily, still amused at the quick change of demeanor.

“As you wish, princess,” Sam joked, hooking his fingers behind the waistband of Jack's boxers, pulling them down swiftly. Jack's face heat up at his words, but his mind clouded over the second his erection slapped up against his stomach. Sam's warm hands left his body to take off his own underwear. “Ready?”

Sam curled his hand around Jack's erection, holding his hips down to keep them from violently bucking up. After moments of holding his hand still and letting Jack adjust, Sam tightened his grip and flicked his wrist upwards. The image in front of him was the most arousing thing he'd ever witnessed, Jack's eyes were closed and his brows furrowed, mouth open to let out all of the delicious sounds from the pleasure. A bead of sweat was rolling down his forehead and his chest flushed a pretty pink. “Ah- Sam, do that again.” Jack cried, thrusting up to chase that feeling again. Complying, Sam started to move his hand in a slow, steady rhythm. His own erection begged for attention, he couldn't deny it any longer. Letting his free hand slip from Jack's hips to his crotch, he matched the movements he was using on Jack on his own cock. 

Both men moaned in unison as Sam working both of their cocks at the same pace. Jack arched his back while he tried to grip at everything he could reach, he fisted the sheets as he begged Sam for more. The electrically charged energy pooling under Jack's skin sent small ripples of pleasure through Sam's body, it made the latter realize how close he was. Jack seemed to notice too, as he raised his hand to stop Sam's motions. “Sam, not yet,” he groaned, and moved away to hold off his orgasm. “Let me touch you.” It was more of a question than a statement, he waited to reach out until he received an approving nod. 

Clumsily wrapping his hand around Sam's cock, Jack gave it an experimental squeeze which elicited a moan from the older man. “Yeah, that's good,” Sam encouraged Jack. “Can you try going up and down?” He bit his lip when Jack did exactly as instructed, a wave of pleasure shooting through his groin. It had been a long time since anyone touched him like that, and he couldn't be happier it was with someone he truly loved. Sam reached down to put his hand on top of Jack's, helping him move his hand to build a steady pace, grunting appreciatively and letting go when Jack got the hang of it. “Oh, that's perfect, Jack.” Sam moaned, squeezing his eyes shut. 

It made Jack feel good knowing he was making Sam feel good, and vice versa. It was a vicious circle of pleasure that neither man could get enough of. Jack worked Sam's cock with one hand and used his other to hold his hand, he tried applying pressure differently and moving at different speeds, watching Sam's facial expressions to learn what he loved the most. Jack's movements speeding up caused Sam's breathing to get more ragged as he slid his hands through Jack's brownish hair.

Wanting to test the waters, Jack decided to try something he'd only seen in videos before. He pressed his lips against the length of Sam's cock, the silky skin made him hum. It felt heavy against his lips, and Jack was intrigued to explore it more. Sam gasped at the feeling, the him to pull at Jack's scalp. The tug made Jack part his lips, allowing the tip to enter his mouth slightly.

“Oh my God,” Sam moaned, wanting to buck up into Jack's mouth but restraining himself. “Shit. Are you okay? You don't have to.”

Jack pulled off. “I want to.” he whispered. He tightened his grip and wetted his mouth some more. His lips formed a tight circle around the head of Sam's cock as he gently sucked to try out what worked best. Sam let out a low groan, loving how Jack was manipulating his body. He let Jack lick and lap at the sensitive organ for a while, it resulted in Sam being a moaning, sweating mess burying half his face in his pillow. He loved how Jack's mouth felt on him, but he needed more friction to achieve orgasm. Sam pulled back from Jack's touch, making his lips release from his cock with a loud pop.

“You did so good, Jack,” Sam panted heavily. He grasped his cock, starting to stroke it himself. “Come here, I'm close,” Jack lied back down next to Sam and let his head rest in the crook of his neck. Sam's free hand snaked up Jack's back and held his neck tightly, keeping him in place. Sam grunted as he was close to orgasming. “Jack… fuck.”

Jack nuzzled his neck, watching as he worked his cock. Sam moaned loudly, jaw falling slack as he hit that last perfect stroke. He rubbed the underside of his cock as he finally reached orgasm. His head shot back, moans strained as his whole body contracted. Jack watched his come pour out onto his stomach, and he rubbed Sam's chest and kissed along his jawline as he was riding out his orgasm. With his eyes still firmly shut he tried to catch his breath.

“You didn't have to stop me.” Jack piped up as Sam rolled over to grab a tissue. Sam nodded as he turned around, meeting bright golden eyes. 

“I know you could've handled it, but this is about you too,” Sam gestured to the prominent erection between Jack's legs while he cleaned himself up. “Next time I'll let you, okay?” Jack nodded slowly, realizing he still hadn't gotten off.

“Will you try it on me too?” Jack asked, wanting to feel Sam's mouth on him in the same way. Sam nodded excitedly, he wouldn't want to stop until Jack was just as satisfied as he was. He motioned for Jack to come closer, pressing a kiss on his lips before spreading apart his thighs. Jack's cock was just as hard as before, a drop of pre-come almost dripping down the head. The head was a dark red, almost angry at the lack of stimulation. Sam was about to change that real quick, positioning himself in front of the Nephilim.

“Tell me if you don't like it.”

“I think I'll like it.”

“Still.”

Sam bent down, grabbing a hold of Jack's erection once more. The motion earned him a sharp gasp, and Jack's bright eyes lit up the room. Sam wasted no time bending down to kiss the base of Jack's cock, working upwards until his lips met the head. Because of Jack's inexperience Sam had to take it slow. He moved his hand along his hardness, listening to the moans from the boy below him. Sam made sure the head of Jack's cock was sufficiently lubricated before moving his mouth down along the length, taking it in little by little. 

“Ah! Sam, that's so-,” Jack cut himself off with a loud whine, squeezing his eyes shut at the sudden pleasure. Sam clasped his fingers halfway around Jack's cock to make sure the younger man could safely thrust up in his throat without choking him. 

This didn't go unnoticed by Jack, he realized he had room to move and made good use of it. He felt Sam's tongue run along the underside of his cock, poking at the slit right on top. The intense feeling made him cry out Sam's name, mewling breathlessly as he gently pistoned his hips upwards. Sam's lips tightened around Jack, his other hand working the base of his cock. 

The combination of Sam's mouth and rough hand on his erection brought Jack close to orgasm. Sam could feel Jack's muscles tighten under the stimulation to the point he was writhing on the bed. “Sam… so close.” Jack whimpered, head thrown back as Sam swallowed him down. Sam made sure to bob his head up and down in a faster pace, giving the Jack the speed he needed to come undone. This technique proved to be effective, Jack wailed out as his whole body stiffened, rocking the bed with the power he emitted. Jack slumped against the bed as the first spurt of come left his body, grunting out Sam's name as he reached the throes of orgasm. Swallowing was something Sam had never done before, but he would do everything for Jack. He didn't mind the taste and gently slowed the pace as Jack's breathing returned to normal.

“Shit.” Jack exhaled when Sam removed himself from his softening cock, feeling guilty he didn't pull away. 

“Language,” Sam muttered, wiping his chin from where the mess got on his face. He could tell Jack was a little embarrassed, he wouldn't even make eye contact. “Everything okay?”

Jack shook his head. “I'm sorry Sam, I didn't mean to do that.” Worry was visible in his eyes when he finally dared to look at Sam again. Sam warned him to not take it too far yet, and what'd Jack do? Upset everyone in the bunker only to come in Sam's mouth. To his surprise Sam didn't mirror his worried expression at all, he was met with soft eyes and a bright smile.

“Are you serious, Jack? I loved it. Don't worry about me,” Sam explained, reaching out to hold Jack's hand. The boy's soft smile made his heart swell, they truly made the right decision to do this. “I promise you it's okay. How do you feel?”

“I'm glad we did this,” Jack sighed, nudging Sam's shoulder with his own. Sam always managed to reassure him, making him feel even more giddy than the strongest orgasm of his life did. “I should probably talk to Dean and Castiel tomorrow. I bet they're still worried.”

Sam scrunched his nose. “Probably, but I don't want to talk about them when we're naked.” His reaction made Jack laugh, quietly agreeing with him. 

“Thank you, Sam. I love you.”

“Love you too, bud. Shower and sleep?”

“Shower and sleep ”


End file.
